Upper Matecumbe Key Travel Guide

Tourist Guide

Islamorada showing a beach bar
Islamorada which includes a beach
Islamorada
Islamorada showing mangroves, a marina and general coastal views
Islamorada showing a sandy beach, tropical scenes and general coastal views
Chesapeake Beach Resort

Chesapeake Beach Resort

3.5 out of 5
83409 Overseas Hwy Islamorada FL
The price is 4.966.154 ₫ per night from 28 Jan to 29 Jan
4.966.154 ₫
7.064.522 ₫ total
28 Jan - 29 Jan
includes taxes & fees
Stay at this beach hotel in Islamorada. Enjoy free breakfast, free Wi-Fi and 2 outdoor pools. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,624 reviews)
Clean, gorgeous view, amazing free breakfast, loved the robes!

Reviewed on 10 Jan 2026

Chesapeake Beach Resort
Cheeca Lodge & Spa

Cheeca Lodge & Spa

5 out of 5
81801 Overseas Highway, Mile Marker 82 Islamorada FL
The price is 7.124.153 ₫ per night from 28 Jan to 29 Jan
7.124.153 ₫
9.935.725 ₫ total
28 Jan - 29 Jan
includes taxes & fees
Stay at this 5-star luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff ...
9.2/10 Wonderful! (1,287 reviews)
Generally nice place. Leftover food and drinks in our hotel refrigerator upon arrival. Understaffed at dining facilities meaning long waits and order mistakes.

Reviewed on 8 Jan 2026

Cheeca Lodge & Spa
Amara Cay Resort

Amara Cay Resort

4 out of 5
80001 Overseas Hwy Islamorada FL
The price is 5.655.727 ₫ per night from 19 Jan to 20 Jan
5.655.727 ₫
8.283.526 ₫ total
19 Jan - 20 Jan
includes taxes & fees
Stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach and 3 bars/lounges. Our guests praise the pool and the helpful staff in their reviews. ...
8.8/10 Excellent! (1,257 reviews)
Na

Reviewed on 8 Jan 2026

Amara Cay Resort
See all 2,793 properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Breezy Palms Resort

Breezy Palms Resort

2.5 out of 5
80015 Overseas Highway Islamorada FL
Stay at this beach aparthotel in Islamorada. Enjoy free Wi-Fi, a beach locale and a marina. Our guests praise the helpful staff and the clean rooms in their ...
8.8/10 Excellent! (606 reviews)
Great location and walkable to restaurants. Clean. Nice beach. Quiet. Pool was heated and warm. This was our first five day stay in a bungalow and we would stay again!

Reviewed on 6 Jan 2026

Breezy Palms Resort
The Islands of Islamorada

The Islands of Islamorada

4 out of 5
82779 Old Hwy Islamorada FL
Stay at this beach villa in Islamorada. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada Brewery ...
9.6/10 Exceptional! (70 reviews)
Beautiful accommodations and location, very clean, many activities available at resort

Reviewed on 25 Nov 2025

The Islands of Islamorada
Treasure Harbor

Treasure Harbor

3 out of 5
200 Treasure Harbor Dr Islamorada FL
Stay at this hotel in Islamorada. Enjoy free Wi-Fi, free parking and premium bedding. Our guests praise the helpful staff in their reviews. Popular attractions ...
8.8/10 Excellent! (123 reviews)
This place is super fun and unlike anywhere we've stayed before. Water lodges are well appointed with all the amenities needed and there are additional facilities around the main reception area.

Reviewed on 6 Jan 2026

Treasure Harbor
See all properties in Upper Matecumbe Key
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Florida Keys Brewing Co.

Florida Keys Brewing Co.

You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada.

Florida Keys Brewing Co.
History of Diving Museum

History of Diving Museum

You can spend an afternoon browsing the exhibits at History of Diving Museum during your travels in Islamorada. Amble around this family-friendly area's seaside and enjoy its lively bars.

History of Diving Museum
Hurricane Monument which includes outdoor art and a monument

Hurricane Monument

3/5(2 reviews)

Learn about the local history of Islamorada when you take a trip to Hurricane Monument. Discover the beautiful sunsets and seafood restaurants in this family-friendly area.

Hurricane Monument

Bud n' Mary's Dive Center

4.5/5(3 reviews)

Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this relaxing area.

Bud n' Mary's Dive Center

Islamorada Brewery & Distillery

You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada.

Islamorada Brewery & Distillery

Keys History & Discovery Center

You can spend time studying the exhibits at Keys History & Discovery Center during your trip to Islamorada.

Keys History & Discovery Center